Why Hiring A Career Coach Was The Best Thing I Ever Did

As the head of client development—and one of the very few women in a managing role—at Smith Barney Morgan Stanley, I had a lucrative career in finance, and 25 years of experience under my belt.

But, in my mid-50s, I was ready for something different.

I'd spent years advising people through their retirements, and I noticed that there were a lot of people in their 80s who'd worked in the same career their entire lives, and then looked back and thought, "Why didn't I do something different? Why did I just keep going down this path?"

The answer: Because it was the easiest thing to do. It was the path of least resistance.

But the path of least resistance wasn't the right one for me.

A Midlife Career Crossroads

My favorite Mark Twain quote comes to mind: "Twenty years from now, you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover."

I was ready to catch those trade winds. But I wasn't ready to retire.

I was in my 50s, with more energy than I had 20 years before, so I had no interest in hitting a ball on a golf course for the rest of my days. I wanted to make a difference in the world—to be fully engaged and use the skills and talents I'd acquired over the years to do something that I was passionate about.

As soon as I made up my mind, I was ready to quit my job and start this new life immediately. That's how I do things—I get fired up and then go full steam ahead. But as I was talking to a friend over coffee about my plan (which wasn't really a plan at all), she told me about New Directions, a company that helps people at my stage of life figure out what to do next. "It's career and retirement coaching," she said. I was skeptical, but I had to admit that I didn't really know where to start.

So I made an appointment. What did I have to lose?

What Career Coaching Is Really Like

At my first meeting, as I was telling the counselor that I was ready to quit my job cold turkey, he responded, "You can always quit, but you can't un-quit."

It was good advice, and I knew at that moment that coaching was something that I could use. I was paired with a counselor, Mark Shepard, M. Div., Th.D., who I met with two to three times a month to begin formulating a proper plan.

For the record, coaching costs anywhere from $15,000 to $75,000, depending on your needs. The New Yorker reported last year that there are close to 50,000 career-cum-retirement coaches out there today. The uptick is likely due to a trend among Baby Boomers known as "retiring retirement"—instead of simply putting their feet up, these folks are pursuing second careers in their later years. In other words, retirement has become a process rather than a destination.

Over the next six months, Mark helped me to understand that walking away from a career—whether you're retiring or just moving on to something else—takes careful thought and consideration. You need time to not only uncover your options, but also do some deep reflecting on who you are and what you're good at. Career coaching is as much about the psychological aspect of changing paths as the financial part.

Along with my coach, I was paired with a psychologist, and we delved back to my childhood years to examine the things I enjoyed and excelled at as a kid. They'll look for the tiniest kernels of joy from your life to see if there's something that might be worth re-engaging with in your coming years.

One thing that we touched upon was my inclination toward nonprofit work. I got my undergraduate degree in urban studies, and my first job out of school was working with an agency that helped the chronically unemployed. I ended up running that agency, but it was so emotionally draining to work with people who were dealing with substance abuse that I shifted into the for-profit sector, with the intent to give back on weekends. That, unfortunately, didn't happen.

Mark also put me through a battery of tests—including four or five written personality tests, like the Myers-Briggs—to really find out what makes me tick. One of the most significant things that I learned about myself was that I'm not someone who can be alone in a cubicle: I get my energy from working with a group of people. I guess I always knew that was true on some level, but the tests confirmed it.

Little did I know that I was about to stumble across an opportunity as far away from a cubicle as you can get.

How I Found the Right Path for Me

The author in Aix-en-Provence, France—her first trip after leaving her job of 25 years.

During this time, I was reading The Big Shift, which mentioned a Harvard fellowship program called the Advanced Leadership Initiative. It's a one-year offering that connects people like me—who've had successful careers in business, and now want to use their skill sets to make a difference in the world—with each other and with Harvard's faculty and staff.

For example, one man in the program is working to bring accessible electricity to Liberia, an African country where only 2,000 households out of 4 million have lights.Another woman in the program has cleaned up San Francisco's unsafe water, and she's even co-authored a book about water and technology.

I finally saw the opportunity I'd always sought to improve the world, so I talked it over with Mark, who agreed that the program would be a good fit for me. When I was accepted, I really was ready to quit my job. I had a plan—I was no longer winging it.

That was more than a year ago, and I just finished the fellowship. I'm now working in an advisory capacity with three different social entrepreneurship startups focused on helping women feel more empowered about managing the financial side of their lives. Thanks to my work with Mark, I have a feeling that, unlike some of my former clients, I'll someday look back on my life and know that I threw off that bowline.

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